Total Synthesis of (−)- and ent-(+)-Vindoline

Younggi Choi, Hayato Ishikawa, Juraj Velcicky, Gregory I. Elliott, Michael M. Miller, and Dale L. Boger*
Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037
Org. Lett., 2005, 7 (20), pp 4539–4542
DOI: 10.1021/ol051975x
Publication Date (Web): August 27, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, boger@scripps.edu

Abstract

Abstract Image

Two exceptionally concise total syntheses of (−)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C−C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.

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History

  • Published In Issue September 29, 2005
  • Received August 15, 2005

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